Mechanism and transition-state structures for nickel-catalyzed reductive alkyne-aldehyde coupling reactions

Journal of the American Chemical Society

Volumn 131, Issue 19, 2009, Pages 6654-6655

  McCarren, P R ^a   Liu, Peng ^a   Cheong, Paul Ha Yeon ^a   Jamison, Timothy F ^b   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACK-DONATION; CHEMICAL EQUATIONS; COUPLING REACTION; LEWIS ACID; OXIDATIVE CYCLIZATION; REDUCTIVE ELIMINATION; TRANSITION STATE; TRANSITION STATE STRUCTURE; TRANSMETALATION;

ALDEHYDES; CHEMICAL BONDS; CYCLIZATION; DENSITY FUNCTIONAL THEORY; NICKEL ALLOYS; OLEFINS; OXYGEN;

ACETYLENE;

ACETYLENE; ALDEHYDE; ALKENE; ALKYNE; BORANE DERIVATIVE; KETONE; LEWIS ACID; NICKEL; PHOSPHINE; TRANSITION ELEMENT;

ARTICLE; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; ELECTRON TRANSPORT; STEREOCHEMISTRY;

EID: 67650514044     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900701g     Document Type: Article

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30. All of the geometry optimizations and frequency calculations were performed with the B3LYP functional implemented in Gaussian 03 (Frisch, M. J.; et al. Gaussian 03, revision D.01; Gaussian, Inc.: Pittsburgh, PA, 2004). The LANL2DZ basis set was used for nickel and the 6-31G(d) basis set for the other atoms.
31. 3) suggested that its transition-state geometries and activation energies are similar to those of the model system (see the Supporting Information for details).
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33. 2 also coordinates with the aldehyde oxygen and accelerates the oxidative cyclization (see the Supporting Information for details).
34. 2 can also accelerate the oxidative cyclization of enone and alkyne in a ligand-free system (see ref 9).
35. See the Supporting Information for the free-energy profile of the full catalytic cycle.
36. For experimental regio- and enantioselectivities, see refs 4d and 5b, c, g-i, l.